We most likely would NOT want to live in the place after being a rental property for 8 years, but again, who knows. The question for me is, are we better off investing that money monthly in tax free bonds, or other investments rather then having the expense of the second home, and possible costs involved, late tenants, repairs, no occupancy, etc?

I did buy a condo in a resort area about 2 years ago with the idea of retiring there. * It came with a tenant who was there the first year I owned it. Then I did a seasonal rental and then I took it back(in May) as a second home, still with the thought of it eventually being primary. It is in an area I have watched for about 20 years, is about 3 hours from my primary home and I have a son and close friend there who are willing to help when I need it.

I bought a short sale townhouse in the same area that closed in May and was on an annual lease before the first mortgage payment was due. It is covering itself. I am in the process of buying a short sale condo that I hope to have in hand before Nov so I can go with an annual or a seasonal lease.

Both the townhouse and the new condo may be rented on a nightly basis if I want to go that route. All I want from these properties is that they cover themselves.

I have stocks,etc and feel like these give me some additional diversity. I wouldn't recommend for everyone and I definitely wouldn't have done it without help right there if I need it. With each thing I buy, I do think "could I live here?" to do a final evaluation.

Just some other thoughts.

*I work about 25% time as a consultant and the lack of flights was all that kept me from moving there permanently. I am doing a business trip leaving from there in August but my daughter,SIL and almost grandson will be moving <hour from my primary home at the end of the year so that does change things again. I'll keep something thataway - at least for awhile.